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Drospirenone, sold under the brand names Yasmin and Angeliq among others, is a progestin medication which is used in birth control pills to prevent pregnancy and in menopausal hormone therapy, among other uses.[4][5] It is available only in combination with an estrogen and is not available alone.[5] The medication is taken by mouth.[4]
Rare side effects of drospirenone may include high potassium levels and blood clots, among others. Drospirenone is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone.[4] It has additional antimineralocorticoid and antiandrogenic activity and no other important hormonal activity.[4] Because of its antimineralocorticoid activity, drospirenone is said to more closely resemble bioidentical progesterone than other progestins.[6][7]
Drospirenone was introduced for medical use in 2.[8] It is available widely throughout the world.[5] The medication is sometimes referred to as a “fourth-generation” progestin.[9][1] It is available as a generic medication.[11]
Drospirenone is an ingredient in some birth control pills and is used in menopausal hormone therapy. In combination with ethinylestradiol it is used as contraception, and for women who want contraception it is also approved by the U.S. Food and Drug Administration (FDA) to treat moderate acne and premenstrual dysphoric disorder.[12] Although FDA-approved, this does come with a higher risk of blood clots than with other contraceptives containing other progestins, and therefore all individuals would have to be individually assessed for appropriateness. Studies have found that the Yaz formulation was superior to placebo in reducing premenstrual emotional and physical symptoms while also improving quality of life.[13]
Angeliq, a drospirenone and estradiol combination, has also been approved by the Food and Drug Administration (FDA) for treatment of moderate to severe vasomotor symptoms and/or vaginal atrophy associated with menopause.[14]
The FDA has several approved indications for combined estrogen and drospirenone preparations. They are approved as a first-line therapy for menopausal symptoms such as the relief of hot flashes.[15] Additionally, they have been shown to reduce the occurrence of bone fractures in postmenopausal women.[16]
Drospirenone is sold as a combined birth control pill under the brand names Yasmin (US, EU, Latin America), Jasmine (France), Yarina (Russia)[17] in a dosage containing drospirenone 3 mg/ethinylestradiol 3 µg. In the United States, Bayer Schering released a pill based on Yasmin with the B vitamin folate (B9), which is marketed under the names Safyral and Beyaz. Worldwide it is also sold under the brand names Yaz and Yasminelle in a lower dosage containing drospirenone 3 mg/ethinylestradiol 2 µg. The drug is also available in combination with estradiol for use in menopausal hormone therapy. Drospirenone is not available on its own (i.e., as a standalone medication).[5]
Drospirenone is a component of oral contraceptive formulations including the following:
In addition to contraindications common to all combined estrogen–progestin medications, drospirenone-containing medications are contraindicated in women with severe renal insufficiency according to European Medicines Agency (EMA)-approved labels,[21] and contraindicated in women with renal insufficiency, adrenal insufficiency, or liver disease according to FDA-approved labels.[22]
Drospirenone is an antimineralocorticoid with potassium-sparing properties, though in most cases no increase of potassium levels is to be expected.[21] In women with mild or moderate renal insufficiency, or in combination with chronic daily use of other potassium-sparing medications (ACE inhibitors, angiotensin II receptor antagonists, potassium-sparing diuretics, heparin, antimineralocorticoids, or nonsteroidal anti-inflammatory drugs), a potassium level should be checked after two weeks of use to test for hyperkalemia.[21][23]
While all oral contraceptives can increase the risk for venous thrombembolic events, including fatal blood clots, several studies have reported a greater risk for women taking contraceptives containing drospirenone. Women who take contraceptive pills containing drospirenone have a 6- to 7-fold risk of developing thromboembolism (dangerous blood clots) compared to women who do not take any contraceptive pill, and have twice the risk (some epidemiological studies suggest thrice, according to the FDA) compared to women who take a contraceptive pill containing levonorgestrel. However, the absolute risk is small, in the neighborhood of 9 to 27 out of 1, women on an oral contraceptive for a year (up to 9 for levonorgestrel vs up to 27 for drospirenone, or about .9% vs .3% per year).[24][25]
When the U.S. Food and Drug Administration (FDA) became concerned about the risks of drospirenone, they funded studies based on the medical records of more than 8, women taking oral contraceptives. They found that the risk of VTE, which includes dangerous and potentially fatal blood clots, was 93% higher for women who had been taking oral contraceptives containing drospirenone for only 3 months or less and 29% higher for women taking drospirenone-containing oral contraceptives for 7 to 12 months, compared to women taking other types of oral contraceptives.[26]
The FDA recently updated the label for contraceptives containing drospirenone to include warnings for stopping use prior to and after surgery, and to warn that contraceptives with drospirenone may have a higher risk of dangerous blood clots.[22]
Drospirenone binds with high affinity to the progesterone receptor (PR) and mineralocorticoid receptor (MR), with lower affinity to the androgen receptor (AR), and with very low affinity to the glucocorticoid receptor (GR).[4][27][28] It is an agonist of the PR and an antagonist of the MR and AR, and hence, is a progestogen, antimineralocorticoid, and antiandrogen.[4][27] Drospirenone has no estrogenic activity and no appreciable glucocorticoid or antiglucocorticoid activity.[4][27] Progestogenic, antimineralocorticoid, and mild antiandrogenic effects have been observed in humans with drospirenone at a dosage of .5 to 4 mg/day.[29]
Drospirenone is an agonist of the PR, the biological target of progestogens like progesterone.[4][27] It has about 35% of the affinity of promegestone for the PR and about 7% of the affinity of progesterone for the PR.[4] Drospirenone has antigonadotropic and al antiestrogenic effects as a result of PR activation.[4][27] The ovulation-inhibiting dosage of drospirenone is 2. mg/day.[4] The medication acts as a contraceptive by activating the PR, which suppresses the secretion of luteinizing hormone, inhibits ovulation, and alters the cervical membrane and endometrium.[3]
Drospirenone is an antagonist of the MR, the biological target of mineralocorticoids like aldosterone, and hence is an antimineralocorticoid.[27] It has about 23% of the affinity of aldosterone and progesterone for the MR.[4] Drospirenone is 8 to 1 times more potent as an antimineralocorticoid than spironolactone.[27][29] As such, 3 mg drospirenone is equivalent to about 2 to 25 mg spironolactone in terms of antimineralocorticoid activity.[31] The antimineralocorticoid activity exhibited by drospirenone promotes sodium excretion and decreases fluid retention.[32] It has been said that the pharmacological profile of drospirenone more closely resembles that of progesterone than other progestins, because its antimineralocorticoid activity is a property that it uniquely shares with progesterone.[27]
Drospirorenone is an antagonist of the AR, the biological target of androgens like testosterone and dihydrotestosterone (DHT).[4] It has about 65% of the affinity of the synthetic anabolic steroid metribolone for the AR.[4] The medication is more potent as an antiandrogen than spironolactone, but is less potent than cyproterone acetate, with about 3% of its antiandrogenic activity.[4][27][29]
The oral bioavailability of drospirenone is between 76 and 85%.[4]Peak levels occur 1 to 2 hours after an oral dose.[4] There is some accumulation in drospirenone levels with continuous administration, with steady-state levels of drospirenone achieved after 7 to 1 days of combined ethinylestradiol and drospirenone therapy.[4] The plasma protein binding of drospirenone is 95 to 97%, with a majority bound to albumin and 3 to 5% circulating freely or unbound.[4] It has no affinity for sex hormone-binding globulin or corticosteroid-binding globulin, and hence is not bound by these plasma proteins.[4] Drospirenone is metabolized by opening of its lactone ring to form an acid grou and by reduction of its double bond between the C4 and C5 positions.[4] The biological half-life of drospirenone is between 25 and 33 hours.[1]
Drospirenone, also known as 1,2-dihydrospirorenone or as 17β-hydroxy-6β,7β:15β,16β-dimethylene-3-oxo-17α-pregn-4-ene-21-carboxylic acid, γ-lactone, is a synthetic steroidal 17α-spirolactone, or more simply a spirolactone.[5][33] It is an analogue of other spirolactones like spironolactone, canrenone, and spirorenone.[5][33] Drospirenone differs structurally from spironolactone only in that the C7α acetylthio substitution of spironolactone has been removed and two methylene groups have been substituted in at the 6β,7β and 15β,16β positions.[34]
The loss of the C7α acetylthio group of spironolactone, a compound with negligible progestogenic activity,[35][36] appears to be involved in the restoration of progestogenic activity in drospirenone, as SC-5233, the analogue of spironolactone without a C7α substitution, has potent progestogenic activity similarly to drospirenone.[37]
Drospirenone was introduced for medical use in 2.[8] It is sometimes described as a “fourth-generation” progestin based on its time of introduction.[9][1]
Drospirenone is the generic name of the drug and its INN, USAN, BAN, and JAN, while drospirénone is its DCF.[5] Its name is a shortened form of the name 1,2-dihydrospirorenone or dihydrospirenone.[5][33] Drospirenone is also known by its developmental code names SH-47 and ZK-3595 (alone), BAY 86-53, BAY 98-771, and SH-T-186D (in combination with ethinylestradiol), and BAY 86-4891 (in combination with estradiol).[5][33][38][39][4][41]
Drospirenone is marketed in combination with an estrogen under a iety of brand names throughout the world.[5] Among others, it is marketed in combination with ethinylestradiol under the brand names Yasmin and Yaz and in combination with estradiol under the brand name Angeliq.[5]
Drospirenone is marketed widely throughout the world.[5]
In July 212, Bayer notified its stockholders that there were more than 12, lawsuits against the company involving Yaz, Yasmin, and other oral contraceptives with drospirenone, and that the company by then settled 1,977 cases for US$42.6 million, for an average of US$212, per case, while setting aside US$61.5 million to settle the others.[42]
As of July 17, 215, there have been at least 4, lawsuits and claims still pending regarding venous thromboembolic events. This doesn’t include the roughly 1, claims that Bayer has already settled without admitting liability. These claims of venous thromboembolic events have amounted to US$1.97 billion. Bayer also reached a settlement for arterial thromboembolic events, including stroke and heart attacks, for US$56.9 million.
[43]
Drospirenone (developmental code name LF-111) is or was under development by Leon Farma as a progestin-only pill for hormonal birth control in women, but as of March 217 no recent reports of development have been identified.[44] The formulation has reached phase III clinical trials for this indication.[44]
Drospirenone (tentative brand name Estelle) is under development by Mithra Pharmaceuticals in combination with estetrol as a combined oral contraceptive for pregnancy in women.[45] As of July 218, it is in phase III clinical trials.[45]
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